Hydrochloric Acid → N-(2-amino-5-fluorobenzoyl)-8-aminocaprylic acid

HRID 343890

反応式

HRID 343890 の反応式
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].[F:18][C:19]1[CH:30]=[C:23]2[C:24](OC(=O)[NH:28][C:22]2=[CH:21][CH:20]=1)=[O:25].Cl>O.O1CCOCC1>[NH2:28][C:22]1[CH:21]=[CH:20][C:19]([F:18])=[CH:30][C:23]=1[C:24]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:25]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 660858-Aminooctanoic acidHCID 2885605-Fluoroisatoic anhydride

生成物 1

HCID 54514696N-(2-amino-5-fluorobenzoyl)-8-aminocaprylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A 50% (by weight) solution of potassium carbonate (11.2 mL, 16.8 mmol, 1.02 eq), 8-aminocaprylic acid (9.5 g, 59.7 mmol, 1.00 eq), 5-fluoroisatoic anhydride (10.82 g, 59.7 mmol, 1.00 eq), dioxane (40 mL), and water (5 mL) were added to a 100 mL round bottom flask equipped with a magnetic stir bar and a condenser. The red cloudy mixture was heated to 90° C. for 2 hours (at which time the reaction was determined, by HPLC, to have finished). The deep purple solution was cooled to 25° C. and acidified to pH=4.0 with 3% (by vol.) aqueous hydrochloric acid. The dark precipitate which formed was isolated by filtration. The solid was recrystallized from 50 mL of 65% ethanol-water, recovered by filtration, and dried over 6 hours in a 50° C. vacuum oven. The N-(2-amino-5-fluorobenzoyl) -8-aminocaprylic acid was isolated as a light yellow solid (11.86 g, 67%), mp=108°-109° C.

後処理

  1. customequipped with a magnetic stir bar and a condenser
  2. temperatureThe deep purple solution was cooled to 25° C.
  3. customThe dark precipitate which formed
  4. customwas isolated by filtration
  5. customThe solid was recrystallized from 50 mL of 65% ethanol-water
  6. filtrationrecovered by filtration
  7. customdried over 6 hours in a 50° C. vacuum oven

出典と根拠

ORDレコード
ord-7f10fbb58d0f47db819aaa186b5b9ccd
出典データセット
uspto-grants-1999_01
特許番号
US05863944

関連ノート

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